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ANILINE                                    149

Properties*—Colourless needles ; in. p. Si '.

/UW/Y/VV/.V.—Add to a solution of phenylhydroxylamine Feh-
linjj's solution and warm. Cuprous oxide is precipitated. To
another portion add amtnoniaca! silver nitrate and warm. Silver
is deposited. See Appendix, p. 276.

Nitrosobenzene...........Dissolve 4 grains of phenylhydroxyl-
amine in the equivalent quantity of ice cold 6 per cent, sulphuric
acid (4 c.c. in 66 c.c. water), and add a well-cooled solution of 4
grams potassium bichromate in 200 c.c. water. Yellow crystals <»f
nitrosobenzene are deposited which distil in the vapour of steam
with an emerald-green colour ; m. p. 67-68''.

C,,Hfi.NHOH + O = C,,H;,NO 4- H,O.

p-Aminophenol.--AcUl gradually i ^ram of phenylhydroxyl-
amine to ro c.c. cone, sulphuric acid and 15 grains of ice, dilute
with 100 c.c. of water and boil. Test a small, sample with bi-
chromate solution in order to see if the smell is that of nitro
bcnxene or quinone. In the latter case conversion is complete.1.
The acid liquid is neutralised with sodium bicarbonate, saturated
with common salt and extracted with ether. On distilling off
the ether, w-amidophcnol crystallises ; m. p. 186".

C,,Iifl.NH.OH •= OIi.C(.II.,.NH,.

PREPARATION  53.
Aniline (Aminobcn/ene ; l*henylamine\ C(;H;,NI1,>
Xinin, AnnafeH, 1842, 44, 2tSj.
50 ^rms. nitrobenzene.
90    „    granulated tin.
170 c,c. cone, hydrochloric add (sp. j^r, ri6'i.
Introduce the tin and nitrobcnxeno into a round flask n.l
litre), and fit it with a straight upright, tube about 2 leet lon^
(air-condenser). Meat the mixture for a few minutes on the
water-bath. Then remove the flask and add the concentrated
hydrochloric acid in quantities of 5 ro c.c. at a time, and shake
repeatedly. The liquid should become hot and boil quietly ;
but, if the action becomes too violent it must be moderated by